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Synthesis of the erythrina alkaloid 3-demethoxyerythratidinone. Novel acid-induced rearrangements of its precursors.

ABSTRACT: [reaction: see text] A new strategy for the synthesis of 3-demethoxyerythratidinone has been developed and is based on an extraordinarily facile intramolecular Diels-Alder reaction of a 2-imido-substituted furan. During the course of the synthesis, several novel acid-induced rearrangement reactions were encountered.

SUBMITTER: Wang Q

PROVIDER: S-EPMC2495026 | biostudies-literature | 2006 Feb

REPOSITORIES: biostudies-literature

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Synthesis of the erythrina alkaloid 3-demethoxyerythratidinone. Novel acid-induced rearrangements of its precursors.

Wang Qiu Q Padwa Albert A

Organic letters 20060201 4

[reaction: see text] A new strategy for the synthesis of 3-demethoxyerythratidinone has been developed and is based on an extraordinarily facile intramolecular Diels-Alder reaction of a 2-imido-substituted furan. During the course of the synthesis, several novel acid-induced rearrangement reactions were encountered. ...[more]

PMID: 16468721

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